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Patented May 28, 1940 QUATERNARY Otto Albrecht, Basel, Switzerland, assignor to the firm Society of Chemical Industry in Basic,

Basel, Switzerland No Drawing. Application April 20, 1935, Serial No. 17,542. In Switzerland April 23, 1934 1 Claim.

any organic radical), i. e., such radicals whichimpart to the CO-group of the general formula x-R.C0.R1 the character of the CO-group of an acyl radical, by treating the compound with a heterocyclic tertiary amine containing at least one six membered ring.

As parent materials there may be named by way of example halogen fatty acids of high molecular weight, for instance, monoor polychloropalmitic acids which contain 1-6 chlorine atoms in the molecule; also tetraor hexa-chloropalmitic acid, (Jr-bromolauric acid, abromomyristic acid, a-bromopalmitic acid, a-bromostearic acid, u-bromomontanic acid, 12bromooctadecen-(9) -acid-(l), a-iodostearic acid, chlorinated or brominated naphthenic or resin acids,

25 as well as salts of these acids. A suitable parent material is provided by an ester of such a carboxylic acid formed from a monoor polyhydric alcohol containing fewer than 6 carbon atoms, for instance methyl-, ethylor amyl-alcohol, glycol, glycerine. Also the amides of the carboxylic acids in question which are substituted at the nitrogen atom by alkyl-, cycloalkylor aryl-radicals, for instance a-bromolauric acid amide, a-bromolauric acid-monomethylamide, 3 a-bromolauric acid-dimethylamide, a-bromostearic acid-'diethylamide, an a-bromopalmitic acid-hydroxyalkylamide, ubromostearic acid anilide, bromostearic acid-2:5-dichloranilide, a-bromostearic ,acid-meta-nitranilide, a-bromo- 40 stearic acid-ortho-methoxyanilide, a-bromolauric acid ethylphenylamide, a bromolauric acidmethylphenylamide, oz-blOll'iOSl288JiC acid-benzylamide, a-bromopalmitic acid-ethylbenzylamide, a-bromostearic acid-benzylphenylamide, and the 45 like, are suitable for the reaction with the tertiary amine. As heterocyclic tertiary amines, "for instance pyridine, quinoline or their homologues. For making the quaternary salts a mixture of the halide with the tertiary amine may be left at 60 rest at ordinary temperature or at raised temperature. The mixture may contain a solvent or a catalyst, for instance finely subdivided copper,

a copper compound or sodium iodide. If one of the reacting components is easily volatile the operation may be conducted under pressure. 5

The quaternary salts made by this invention therefore correspond to the general formula in which R represents an aliphatic hydrocarbon radical having at least 8 carbon atoms, R1 a radical which imparts to the C=O-group the character of the CO-group of an acyl radical, R2 the radical of a heterocyclic quaternary ammonium compound containing at least one six membered ring linked by its N-atom to halogen and to R of the radical These quaternary salts have capillary active properties which make them suitable for applicag tion as textile assistants, for example as agents Example 1 40 5 parts of a-bromostearic acid-ethylester are heated together with 10 parts of pyridine for 2 hours on the boiling water-bath. After distilling the excess of pyridine there is obtained a viscid oil which is dissolved by water to a clear solution of very low surface tension, which foams strongly when shaken. In similar manner the a-bromolauric acid-ethylester or the a-bromopalmitic acid may be converted into the quaternary I H OHa-(CHahu-C-C-Q-CaHs stearic acid-ethylester.

0 from the mother liquor.

For making fast to water a dyeing of 2 per cent. strength, produced by Cotton Yellow CH (Schultz Farbstoiftabellen, 7th edition, No. 726) on cotton piece-goods, the dyed material is treat ed with a solution which contains 1 per cent. calculated onthe weight of the fibrous material, of the pyridinium bromide made from a-blOIi'iO- After 20 minutes, the goods are wrung out and dried. The blue-dyed piece-goods do not bleed in cold water.

Example 2 1 part of a-bromostearic acid-amide, obtainable by the introduction of u-bromostearic acidbromide into an excess of a solution of ammonia, is heatedtogether with 1 part of pyridine for 1 hour in the boiling water-bath. After cooling, the precipitate which has separated is filtered The powder thus obtained dissolves to a clear solution in water, which foams strongly when shaken. The new compound.

corresponds to the formula For softening viscose artificial silk the latter is treated for 20 minutes in a bath containing per liter 0.2 gram of the pyridinium-bromide made as pyridinium-bromide made asv described in this example; the 'wool is entered at 60 C. and the bath is heated within 20 minutes to boiling and boiling is continued for 1 /2 hours. The goods are rinsed and dried and then show a -level dyeing deeper than that obtainable under the same conditions without the added pyridinium bromide.

Example 3 10 parts of a-bromostearic acid and 20 parts of pyridine are heated together on the boiling water-bath until the product of the reaction is soluble in water, whichoccurs in about 1 hour. When the pyridine has been distilled there is obtained a powder suitable for making fast to water cotton dyeings or for softening artificial silk. The new compound corresponds to the formula (I!!! ne on Example 4 A solution of 60 parts of a-bromostearic acidbromide in about 100 parts of benzene, at a temperature below 20 C., is dropped gradually into 27.5 parts of aniline diluted with about 100 parts of benzene. After standing for several hours the product which has separated is filtered from the mother liquor by suction, washed with benzene and dried. The a-bromostearic acidanilide, from which aniline-hydrobromide has been removed by washing with water, is, when dry, a nearly colorless powder. It corresponds to the formula For converting it into the quaternary pyridinium salt the anilide is heated together with twice its weight of pyridine on the boiling water-bath until a product soluble in water is obtained. The mass is then'diluted with water and evaporated to dryness, preferably under diminished pressure. There remains a tough mass the aqueous solution of which foams strongly when shaken.

For making fast to water a dyeing of 2.5 per cent. strength of Chlorantin Light Red 53L (Schultz, Farbstoiftabellen, 7th edition, vol. II, page 48) on cotton piece-goods, thelatter are treated after the dyeing with a solution of 0.75

per cent. of the pyridinium bromide obtained.

from a-bromostearic acid-anilide, calculated on the weight of the fibrous material. After 20 minutes the goods are wrung out and dried.

They do not bleed in cold water.

Example 5 (N A solution of 68 parts of m-bromolauric acidbromide in about 60 parts of benzene, vata temperature below about 20 0., is dropped gradually into 41 parts of aniline diluted with 79 parts of benzene. "The product separates from the solution allowed to stand overnight; it is collected on a suction filter,. washed with hen.-

\ zerre and dried. When separated from aniline What I claim is: which product is a Water-soluble powder whose The quaternary ammonium salt of the general aqueous solutions have capillary active properformula ties, and which is capable of rendering the dyef ings of direct dyeing dyestufis fast to water by CHa(CHa)9C-C-N after-treatment.

O'I'IO ALBRECHT. N-lmlogen CeHa 11 (DH HG CH 

